TY - JOUR
T1 - Chelation-controlled asymmetric aminohalogenation reaction
AU - Wang, Yi Ning
AU - Kattuboina, Adiseshu
AU - Ai, Teng
AU - Banerjee, Diya
AU - Li, Guigen
N1 - Funding Information:
We gratefully acknowledge the Robert A. Welch foundation (D-1361) for its generous support of this work. We thank Mr. David W. Purkiss for his assistance in NMR analysis and Eileen Duesler (University of New Mexico) for assistance in X-ray analysis.
PY - 2007/10/29
Y1 - 2007/10/29
N2 - The chelation-controlled asymmetric aminohalogenation of α,β-unsaturated 3-aryl-N-acyl-N-4-phenyl-2-oxazolidinones have been established by using palladium(II) acetate as the catalyst and as the chelation metal. The reaction is very convenient to perform by simply mixing the three reactants, cinnamates, N,N-dichloro-p-toluenesulfonamide and catalyst together with 4 Å molecular sieves at rt in any convenient vial of appropriate size without special protection from inert gases. Unlike the previous asymmetric aminohalogenation, the ionic liquid, [BMIM][NTf2], was found to be superior to [BMIM][BF4] as the reaction media. It was also found that palladium(II) acetate has to be used together with 1 equiv of MeCN to achieve the opposite chelation control. The resulting absolute stereochemistry of the product was unambiguously determined by X-ray structural analysis.
AB - The chelation-controlled asymmetric aminohalogenation of α,β-unsaturated 3-aryl-N-acyl-N-4-phenyl-2-oxazolidinones have been established by using palladium(II) acetate as the catalyst and as the chelation metal. The reaction is very convenient to perform by simply mixing the three reactants, cinnamates, N,N-dichloro-p-toluenesulfonamide and catalyst together with 4 Å molecular sieves at rt in any convenient vial of appropriate size without special protection from inert gases. Unlike the previous asymmetric aminohalogenation, the ionic liquid, [BMIM][NTf2], was found to be superior to [BMIM][BF4] as the reaction media. It was also found that palladium(II) acetate has to be used together with 1 equiv of MeCN to achieve the opposite chelation control. The resulting absolute stereochemistry of the product was unambiguously determined by X-ray structural analysis.
KW - 4-Phenyl-2-oxazolidinone
KW - Aminohalogenation
KW - Ionic liquids
KW - Palladium(II) acetate
UR - http://www.scopus.com/inward/record.url?scp=35448944814&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2007.08.099
DO - 10.1016/j.tetlet.2007.08.099
M3 - Article
AN - SCOPUS:35448944814
SN - 0040-4039
VL - 48
SP - 7894
EP - 7898
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 44
ER -